methyl (Z)-7-[(1S,2R,3R,5S)-3-(1-ethoxyethoxy)-2-[(E,3R)-3-(1-ethoxyethoxy)oct-1-enyl]-5-hydroxycyclopentyl]hept-5-enoate | 1220119-06-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-7-[(1S,2R,3R,5S)-3-(1-ethoxyethoxy)-2-[(E,3R)-3-(1-ethoxyethoxy)oct-1-enyl]-5-hydroxycyclopentyl]hept-5-enoate
• CAS: 1220119-06-1
• 化学式: C₂₉H₅₂O₇
• 分子量: 512.728
• InChiKey: WJNDIYMHNFMKAB-AATKACERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (Z)-7-[(1S,2R,3R,5S)-3-(1-ethoxyethoxy)-2-[(E,3R)-3-(1-ethoxyethoxy)oct-1-enyl]-5-hydroxycyclopentyl]hept-5-enoate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Total Synthesis of 15-D_2t- and 15-epi-15-E_2t-Isoprostanes

  摘要：

  The first total synthesis of 15-D-2t-isoprostane is described. (-)-(9S, 15S)-15-D-2t-IsoP 1 and (+)-(11R, 15R)-15-epi-15-E-2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.

  DOI：

  10.1021/jo1000274
• 作为产物：
  描述：

  methyl (Z)-7-[(1S,2R,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-(1-ethoxyethoxy)-2-[(E,3R)-3-(1-ethoxyethoxy)oct-1-enyl]cyclopentyl]hept-5-enoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到methyl (Z)-7-[(1S,2R,3R,5S)-3-(1-ethoxyethoxy)-2-[(E,3R)-3-(1-ethoxyethoxy)oct-1-enyl]-5-hydroxycyclopentyl]hept-5-enoate
  参考文献：
  名称：

  Total Synthesis of 15-D_2t- and 15-epi-15-E_2t-Isoprostanes

  摘要：

  The first total synthesis of 15-D-2t-isoprostane is described. (-)-(9S, 15S)-15-D-2t-IsoP 1 and (+)-(11R, 15R)-15-epi-15-E-2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.

  DOI：

  10.1021/jo1000274